Chemical substance record

Hypaphorine

487-58-1C₁₄H₁₈N₂O₂246.31 g/mol

Organic/Inorganic Small MoleculeChEBI source record

An amino acid betaine obtaine by exhaustive methylation of the α-amino group of L-tryptophan with concomitant deprotonation of the carboxy group. — ChEBI

Safety references

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Identity & molecular properties

Source-linked values

CAS number	487-58-1	ChEBI ↗
Molecular formula	C₁₄H₁₈N₂O₂	ChEBI ↗
Molar mass	246.31 g/mol	ChEBI ↗
Monoisotopic mass	246.13683 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:5832	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	246.30 g/mol	PubChem ↗
Exact mass	246.136827821 Da	PubChem ↗
Computed XLogP	2.9	PubChem ↗
Topological polar surface area (Å²)	55.9	PubChem ↗
H-bond donors	1	PubChem ↗
H-bond acceptors	2	PubChem ↗
Rotatable bonds	3	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

hypaphorine

IUPAC name

(2S)-3-(1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate

InChIKey

AOHCBEAZXHZMOR-ZDUSSCGKSA-N

SMILES

C[N+](C)(C)[C@@H](Cc1cnc2ccccc12)C(=O)[O-]

InChI

InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1

Names & synonyms

(2S)-3-(1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

amino-acid betaineChEBI parent class · 22860 ↗indole alkaloidChEBI parent class · 38958 ↗L-tryptophan derivativeChEBI parent class · 47994 ↗

organic molecular entity

Roles recorded in ChEBI

xenobioticplant metabolitefungal metabolite

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00405992 mol

Uses 246.31 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 14 atoms

68.27%

O

Oxygen · 2 atoms

12.99%

N

Nitrogen · 2 atoms

11.37%

H

Hydrogen · 18 atoms

7.37%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Hypaphorine from the ectomycorrhizal fungus Pisolithus tinctorius counteracts activities of indole-3-acetic acid and ethylene but not synthetic auxins in eucalypt seedlings. ↗Molecular plant-microbe interactions : MPMI · 2000 Feb · PMID 10659705

Root hair elongation is inhibited by hypaphorine, the indole alkaloid from the ectomycorrhizal fungus Pisolithus tinctorius, and restored by indole-3-acetic acid. ↗Planta · 2000 Oct · PMID 11089686

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:5832

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 442106 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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